In my last post, I explored the idea behind pro bono financial advice and how that idea of a “Second Mountain” has started to resonate with me in a way it probably wouldn’t have a few years ago. At some point, though, those thoughts have to move beyond reflection. You can only carry an idea around in your head for so long before you have to say it out loud and see what happens. For me, that took a little longer than it probably should have.
As I’ve said, the idea itself had been forming for a while. I wanted to participate in what I was initially calling financial literacy. Not financial literacy in the traditional sense, not teaching in a classroom, but real pro bono financial advice for people who simply don't have a way to get it. The idea stayed mostly internal for a while. Part of that was just wanting to be sure I believed in it enough to act on it part of it was proving to myself that I could “pass the test”. Part of it, if I’m honest, was not really knowing how it would land once I said it out loud.
Comfortable isn’t always satisfied
Around the same time, I was comfortable and settled in with my role at Diversified. I had joined in what I’ve always viewed as a bit of a hybrid role, taking to advisors on growth, succession, and the kinds of transitions that naturally come after spending a career building something. It’s work I’ve been close to for a long time, and something I enjoy. I had also known Diversified and the leadership team for years, which made the transition feel pretty natural. There’s a culture there that feels different, more aligned around people than process, and that mattered to me. Still, this idea I had been carrying around felt like something separate. It wasn’t part of the role I was brought in to do, and I hadn’t fully figured out what it could become.
Eventually, as we got into the late fall, I decided it was time to stop thinking about it and actually talk about it. I had a call with Andrew Rosen and Mike Fisher and tried to put into words something that, up to that point, I had only really worked through in my own head. I’m not sure I said it perfectly, and I’m pretty sure I hadn’t said it more than a handful of times before that conversation. What stood out to me wasn’t how I said it, but how quickly they responded.
There wasn’t much hesitation. The reaction was essentially, “Yes, we should be part of this. And if you want to take the lead on it, we’ll support you.” Not as a side effort, not as something to check a box, but as something worth building over time. I walked out of that conversation feeling validated, and honestly, a little honored. It’s one thing to believe in an idea yourself. It’s another thing to have people you respect, hear it, understand it, and want to stand behind it with you.
And for the record, when I passed the CFP exam, they also sent along a great bottle of anejo tequila as a “congratulations”, which felt like an appropriate way to mark the moment (and to prove they know me all to well). What that conversation really did was shift this from something that was theoretical into something that could actually take shape.
Parallel paths
When I step back and look at it, we have a lot of the pieces in place. We have advisors who care deeply about the work they do and who I believe would want to be part of something like this. We have team members and planners who may be looking for ways to contribute beyond their day-to-day responsibilities. We have offices, infrastructure, and the ability to deliver real financial advice in a thoughtful way. And we have access to organizations like the Foundation for Financial Planning, who have already built resources and frameworks to help guide efforts like this. That doesn’t mean it’s simple.
If anything, it just means the real work is beginning. We’re now asking the questions that actually matter. What should these engagements look like? Is there a niche each office will want to support? How much time should our advisors commit? How do we structure this in a way that is sustainable, meaningful, and done right? Those aren’t small questions, and we don’t have all the answers yet.
But what matters to me is that we’re asking them, and that we’re doing it with intention. This is no longer just an idea sitting in the background. It’s something we’re actively working on, alongside everything else that comes with serving clients and running a business. I’m grateful to be doing it in a place that sees the value in it and is willing to invest the time and energy to get it right.
And if you’re reading this and have had even a passing thought about doing something similar personally or in your own firm, I am going to keep sharing what I’m learning as we go down this parallel path. I have to believe that there are others, like me, that were (or still are) in the financial services world that are interested in doing more.